Anna Maria Island Rentals
39 properties available
Welcome to Sandy Pants!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.2150 sq. ft.HIGHLIGHTS:- Kitchen, Dining, Living w/ TV- 1 King Bedroom - 1 Queen Bedroom - 1 Custom Bunk Room w/ 3 Twin Beds and 2 Double Beds- Sleeper SofaPool Area
Sandy Pants
Holmes Beach
$355.00 - $900.00 / per night
3
bedrooms
2
baths
8
guests
5
(33)
Welcome to La Buena Vida!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The waterfront 3-bedroom home has a private heated pool, spa, and dock! This home's location is second to none, just steps to the bayside beaches and easy walking distance to B
La Buena Vida
Anna Maria
$380.00 - $980.00 / per night
3
bedrooms
3
baths
8
guests
5
(1)
Welcome to Island Girl West!On Anna Maria Island (Holmes Beach, Florida)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.A spectacular vacation half-duplex that promises an unparalleled escape on Anna Maria Island.HIGHLIGHTS:- Short Walk to Beach- Kitchen, Dining, Indoor/Outdoor Living
Island Girl West
Holmes Beach
$225.00 - $600.00 / per night
2
bedrooms
2
baths
5
guests
5
(2)
Welcome to Tern Key!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated vacation rental agency.Pristine Newly Built Spacious Luxury Canal Front Home with Pool, Spa, Dock, Close to Bean Point Beaches & Downtown Anna Maria, Bikes Included!3650 sq. ft.HIGHLIGHTS:- Private Single Family H
Tern Key
Anna Maria
$560.00 - $2,200.00 / per night
4
bedrooms
4
baths
8
guests
5
(5)
Welcome to Serenity Now!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated vacation rental agency.HIGHLIGHTS:- Open layout and spacious Kitchen, Dining, Living w/ TV, Covered Porch/Balcony off living area- 1 King Bedroom w/ TV, En-Suite Full Bathroom (shower, tub, double sink), Walk-in
Serenity Now
Holmes Beach
$380.00 - $1,450.00 / per night
4
bedrooms
3
baths
8
guests
5
(4)
Welcome to Island Girl East & West!On Anna Maria Island (Holmes Beach, Florida)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Introducing Island Girl East & West, an extraordinary duplex that guarantees an unforgettable escape to Anna Maria Island.HIGHLIGHTS:- Expansive tropical p
Island Girl - East & West
Holmes Beach
$340.00 - $980.00 / per night
4
bedrooms
4
baths
10
guests
5
(3)
Welcome to Sol Mate!On Anna Maria Island (Anna Maria, FL)Managed locally by Once Upon A Beach Vacation Rentals & Property ManagementBeautifully updated, fresh, and clean elevated 3 Bed, 2.5 Bath which sleeps up to 8 within easy walking distance to Bean Point beaches & Close to Anna Maria's Beloved Pine Avenue1500 square feetHIGHLIGHTS:-
Sol Mate
Anna Maria
$324.00 - $880.00 / per night
3
bedrooms
2
baths
8
guests
5
(9)
Welcome to On Turtle Time!On Anna Maria Island (Holmes Beach, Florida)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Beautifully Recently Updated Ground Level Home w/ Private Pool in Holmes Beach, 6-8 min walk to beachHIGHLIGHTS:- Kitchen, Dining, Living w/ Queen Sleeper Sofa & TV- 1
On Turtle Time
Holmes Beach
$220.00 - $700.00 / per night
2
bedrooms
2
baths
6
guests
5
(3)
Welcome to Point's Hideaway!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.HIGHLIGHTS:- Kitchen, Dining, Living w/ TV- 1 King Bedroom w/ TV, En-Suite Full Bathroom w/Walk in Shower- 1 King Bedroom w/ TV, En-Suite Full Bathroom w/Shower Tub Combo- 1
Point's Hideaway
Anna Maria
$324.00 - $880.00 / per night
3
bedrooms
3
baths
8
guests
5
(5)
Welcome to AMI Peppertree Paradise!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.1970 sq. ftHIGHLIGHTS:- Kitchen, Dining Area, Living w/ TV- 1 King Bedroom w/ TV and Ensuite Full Bath & Walk-In Closet- 1 Queen Bedroom w/ TV- 2 Bunk Beds w/Trundle
AMI Peppertree Paradise
Anna Maria
$310.00 - $880.00 / per night
3
bedrooms
2
baths
8
guests
5
(2)
Welcome to Anna Maria Aloha!On Anna Maria Island (Anna Maria, Florida)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Renovated, Designer Inspired, Ground Level Home on Beach Block Just Steps to Pristine Beaches of Anna Maria Island!HIGHLIGHTS:- Fully Equipped Kitchen, Dining, Living Room
Anna Maria Aloha
Anna Maria
$250.00 - $650.00 / per night
3
bedrooms
2
baths
6
guests
5
(8)
Welcome to Bateman's!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.2543 sq. ft.HIGHLIGHTS:- Open layout and spacious Kitchen, Dining, Living w/ TV- 1 King Bedroom w/ TV, En-Suite Full Bathroom- 1 King Bedroom w/ TV, En-Suite Full Bathroom- 1 King
Bateman's
Anna Maria
$560.00 - $2,200.00 / per night
4
bedrooms
4
baths
8
guests
5
(11)
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